Triethylamine → Ethyl pyrimidine-4-carboxylate

HRID 2063339Notes

Reaction equation

HRID 2063339 reaction equation
C(N(CC)CC)C.Cl[C:9]1[N:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[C:11](Cl)[N:10]=1>O1CCCC1.[C].[Pd]>[N:10]1[CH:11]=[CH:12][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:14][CH:9]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 13341900Ethyl 2,6-dichloropyrimidine-4-carboxylate2×

Product 1

HCID 13639438Ethyl pyrimidine-4-carboxylateYield 86,605.898%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (48.03 g, 0.475 mmol) was added to a solution of ethyl 2,6-dichloropyrimidine-4-carboxylate (intermediate 4, 38.60 g, 0.175 mmol) in tetrahydrofuran (700 ml). The solution was added with Palladium-carbon(5%), and stirred under a hydrogen atmosphere for 6 hours. The solid in the reaction system was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give ethyl pyrimidine-4-carboxylate (intermediate 5, 23.06 g, 87%).

Workup

  1. customThe solid in the reaction system was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f6421b137fb44296a74ce230076a4a2f
Source dataset
uspto-grants-2012_10
Patent number
US08288383B2

Reaction notes

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